Hello Jeff. First you can read up on
types of headphones. Second you should consider that like MI cabinets, even the good ones need a good amp to deliver their potential; so a good headphone amplifier should be on your list. Lastly you can add my concrete suggestions to any you get from others:
Currently I have no application for any type of headphones except open. Some time ago, I gave up on Sennheiser because they are designed to break and cannot be repaired.
For critical listening, and for raw, alive-sounding audio, I have a pair of
Grado SR 225e. They are supra-aural and not the most comfortable. But I can wear them for up to a few hours at a time. I just replaced the ear pads on my set after more than three years. Probably I should have done that after a year or two. The SR 225e may be at or near the bottom of the Grado line, but man can they present the sound of a bass guitar and preamp with authority and detail. Visceral and real-sounding. Also efficient and very responsive. My first and lasting impression of these phones is of them sounding akin to grand, old home stereo speakers, like my remanufactured large Advents.
Just before I replaced the Grado ear pads, I got a pair of
AKG K 240 Mk II. They are circumaural and are very comfortable. I got this pair because recently I assembled a modular synthesizer. Despairing of the then old Grado ear pads, I decided to refurbish the Grado pair and keep it as my main phones for bass guitar and critical listening, while having the AKG phones for long synthesis sound design sessions. I find the AKG K 240 Mk II to sound polite, detached, and accurate. Lifeless by comparison to the Grado phones, they are notoriously inefficient and commensurately not very responsive. But I think this is why so many people like them: they have no personality and simply sound good. And they do basically sound good. Also I can wear them for any length of time without discomfort or (so far) ear fatigue.